Ethyl propanecarboximidate hydrochloride → N'-(4-methyl-1H-pyrazol-5-yl)propanimidamide;hydrochloride

HRID 2260048Notes

Reaction equation

HRID 2260048 reaction equation
[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][NH:4][N:3]=1.[ClH:8].[C:9](=[NH:15])(OCC)[CH2:10][CH3:11]>C(#N)C>[ClH:8].[CH3:7][C:6]1[C:2]([NH:1][C:9](=[NH:15])[CH2:10][CH3:11])=[N:3][NH:4][CH:5]=1

Participants

4

Reactant 2

HCID 13000588Ethyl propanecarboximidate hydrochlorideHCID 178430915HCID 178430915, compound

Product 1

HCID 178458055N'-(4-methyl-1H-pyrazol-5-yl)propanimidamide;hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 8.06 g portion of 3-amino-4-methyl-1H-pyrazole was dissolved in 30 ml of acetonitrile and, with cooling on an ice bath, 12.9 g of ethyl propionimidate hydrochloride was added to the solution. The resulting mixture was stirred for 1 hour at the same temperature and then overnight at room temperature. After removing insoluble materials by filtration, the resulting filtrate was concentrated under a reduced pressure, and the thus obtained residue was subjected to silica gel column chromatography. Elution with methanol-chloroform (1:9-3:7, v/v) gave 8.40 g of N-(4-methyl-1H-pyrazol-3-yl)propionamidine hydrochloride.

Workup

  1. temperaturewith cooling on an ice bath
  2. customovernight
  3. customat room temperature
  4. customAfter removing insoluble materials
  5. filtrationby filtration
  6. concentrationthe resulting filtrate was concentrated under a reduced pressure
  7. washElution with methanol-chloroform (1:9-3:7

Sources & evidence

ORD record
ord-dc7bb7921f7b4c8387a70af0df9ab599
Source dataset
uspto-grants-1995_12
Patent number
US05475114

Reaction notes

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